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P49007

Sigma-Aldrich

Piperine

≥97%

Synonym(s):

(E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide, 1-Piperoylpiperidine

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About This Item

Empirical Formula (Hill Notation):
C17H19NO3
CAS Number:
94-62-2
Molecular Weight:
285.34
Beilstein:
90741
EC Number:
202-348-0
MDL number:
MFCD00005839
UNSPSC Code:
12352100
PubChem Substance ID:
24898568
NACRES:
NA.22

Assay

≥97%

form

crystalline
powder, crystals or chunks
solid

mp

131-135 °C (lit.)

SMILES string

O=C(\C=C\C=C\c1ccc2OCOc2c1)N3CCCCC3

InChI

1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

InChI key

MXXWOMGUGJBKIW-YPCIICBESA-N

Gene Information

human ... CYP3A4(1576)

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Application

Reactant for synthesis of:
  • Dimeric amide alkaloids
  • Piperoyl-amino acid conjugates used for antileishmanial activity
  • Piperine derived amides with TRPV1 activity
  • Piperine analogues as S. aureus NorA efflux pump inhibitors
  • Bioactive conjugates of curcumin with antimicrobial and antiproliferative properties
  • Piperine derivatives for use as trypanocidal agents

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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V. R. S. Rao, et al.,
Tetrahedron, 67, 1885-1892 (2011)
Janine Zaugg et al.
Journal of natural products, 73(2), 185-191 (2010-01-21)
A plant extract library was screened for GABA(A) receptor activity making use of a two-microelectrode voltage clamp assay on Xenopus laevis oocytes. An ethyl acetate extract of black pepper fruits [Piper nigrum L. (Piperaceae) 100 microg/mL] potentiated GABA-induced chloride currents
Jiu-Wang Yu et al.
Molecular diversity, 25(1), 233-248 (2020-03-05)
Piperine is the main active component of Piper longum L., which is also the main component of anti-sciatica Mongolian medicine Naru Sanwei pill. It has many pharmacological activities such as anti-inflammatory and immune regulation. This paper aims to preliminarily explore
Paul B Yaffe et al.
Experimental and molecular pathology, 94(1), 109-114 (2012-10-16)
Piperine, an alkaloid phytochemical found in the fruit of black and long pepper plants, is reported to inhibit the growth of cancer cells; however, the mechanism of action in human cancer cells is not clear. In this study we investigated
Sophia Khom et al.
Biochemical pharmacology, 85(12), 1827-1836 (2013-04-30)
The action of piperine (the pungent component of pepper) and its derivative SCT-66 ((2E,4E)-5-(1,3-benzodioxol-5-yl))-N,N-diisobutyl-2,4-pentadienamide) on different gamma-aminobutyric acid (GABA) type A (GABA(A)) receptors, transient-receptor-potential-vanilloid-1 (TRPV1) receptors and behavioural effects were investigated. GABA(A) receptor subtypes and TRPV1 receptors were expressed in
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